Benzoyl Peroxide → HCID 14835358, compound

HRID 1198993Notes

Reaction equation

HRID 1198993 reaction equation
[CH2:1]([C:3]1[C:11]2[C:7](=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:2].[Br:18]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:18][CH:1]([C:3]1[C:11]2[C:7](=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14835357HCID 14835357, compound

Product 1

HCID 14835358HCID 14835358, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 12.2 g (0.054 mole) of 7-ethyl-3-phenyl-2,1-benzisoxazole in 60 ml of carbon tetrachloride was added 10.5 g (0.059 mole) of N-bromosuccinimide and 0.1 g of dibenzoylperoxide. The stirred reaction mixture was heated at reflux under flood light illumination and an argon atmosphere for 2.5 hr. The cooled reaction mixture was filtered and the filter cake was washed with 40 ml of carbon tetrachloride. The combined filtrates were washed with three 100 ml portions of 10% sodium bicarbonate, twice with 100 ml portions of water and dried over sodium sulfate. The sodium sulfate was removed by filtration, the filtrate was treated with charcoal and filtered. The filtrate was concentrated to give 16.2 g (98%) of slightly impure title compound as a light brown oil that solidified upon standing. A sample was recrystallized from diethyl ether-petroleum ether (30°-60° C.) to give yellow crystals, m.p. 73°-77° C.

Workup

  1. customThe stirred reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux under flood light illumination
  4. customThe cooled reaction mixture
  5. filtrationwas filtered
  6. washthe filter cake was washed with 40 ml of carbon tetrachloride
  7. washThe combined filtrates were washed with three 100 ml portions of 10% sodium bicarbonate, twice with 100 ml portions of water
  8. dry with materialdried over sodium sulfate
  9. customThe sodium sulfate was removed by filtration
  10. additionthe filtrate was treated with charcoal
  11. filtrationfiltered
  12. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-6617dc86beec4058bd6409c5b7ce9218
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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